DE1620057C3 - Substituierte 3-(5-Phenyl-2-tetrazolyl)-propionsäuren und Verfahren zu deren Herstellung - Google Patents
Substituierte 3-(5-Phenyl-2-tetrazolyl)-propionsäuren und Verfahren zu deren HerstellungInfo
- Publication number
- DE1620057C3 DE1620057C3 DE1620057A DEM0071989A DE1620057C3 DE 1620057 C3 DE1620057 C3 DE 1620057C3 DE 1620057 A DE1620057 A DE 1620057A DE M0071989 A DEM0071989 A DE M0071989A DE 1620057 C3 DE1620057 C3 DE 1620057C3
- Authority
- DE
- Germany
- Prior art keywords
- tetrazolyl
- acid
- phenyl
- substituted
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- GLOFATPXSACMFD-UHFFFAOYSA-N 3-(5-phenyltetrazol-2-yl)propanoic acid Chemical class OC(=O)CCN1N=NC(C=2C=CC=CC=2)=N1 GLOFATPXSACMFD-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- MARUHZGHZWCEQU-UHFFFAOYSA-N 5-phenyl-2h-tetrazole Chemical compound C1=CC=CC=C1C1=NNN=N1 MARUHZGHZWCEQU-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FYTWOPWWZQRBEH-UHFFFAOYSA-N 3-[5-(3,4-dichlorophenyl)tetrazol-2-yl]propanoic acid Chemical compound OC(=O)CCN1N=NC(C=2C=C(Cl)C(Cl)=CC=2)=N1 FYTWOPWWZQRBEH-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 210000000416 exudates and transudate Anatomy 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 229960000380 propiolactone Drugs 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical group O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- GHFHGRCLLWAJBT-UHFFFAOYSA-N 3-[5-(4-chlorophenyl)tetrazol-2-yl]propanoic acid Chemical compound OC(=O)CCN1N=NC(C=2C=CC(Cl)=CC=2)=N1 GHFHGRCLLWAJBT-UHFFFAOYSA-N 0.000 description 1
- SPKVZXBNWCKHGR-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)-2h-tetrazole Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=NNN=N1 SPKVZXBNWCKHGR-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 101100409194 Rattus norvegicus Ppargc1b gene Proteins 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- FQTIYMRSUOADDK-UHFFFAOYSA-N ethyl 3-bromopropanoate Chemical compound CCOC(=O)CCBr FQTIYMRSUOADDK-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- -1 propionic acid nitrile Chemical class 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F23—COMBUSTION APPARATUS; COMBUSTION PROCESSES
- F23K—FEEDING FUEL TO COMBUSTION APPARATUS
- F23K3/00—Feeding or distributing of lump or pulverulent fuel to combustion apparatus
- F23K3/10—Under-feed arrangements
- F23K3/14—Under-feed arrangements feeding by screw
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Mechanical Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Combustion & Propulsion (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51359965A | 1965-12-13 | 1965-12-13 | |
| US513553A US3412193A (en) | 1965-12-13 | 1965-12-13 | 11-(4-methyl-1-piperazinyl)dibenz[b, f][1, 4]oxazepines or thiazepines for controlling fertility |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1620057A1 DE1620057A1 (de) | 1970-03-19 |
| DE1620057B2 DE1620057B2 (de) | 1977-10-06 |
| DE1620057C3 true DE1620057C3 (de) | 1978-06-08 |
Family
ID=27057915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1620057A Expired DE1620057C3 (de) | 1965-12-13 | 1966-12-12 | Substituierte 3-(5-Phenyl-2-tetrazolyl)-propionsäuren und Verfahren zu deren Herstellung |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3412193A (enExample) |
| BE (1) | BE691049A (enExample) |
| CH (1) | CH476001A (enExample) |
| DE (1) | DE1620057C3 (enExample) |
| FR (1) | FR1504326A (enExample) |
| GB (1) | GB1129393A (enExample) |
| NL (1) | NL6617500A (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL140242B (nl) * | 1963-03-01 | 1973-11-15 | Wander Ag Dr A | Werkwijze voor het bereiden van op de 11-plaats door een basische groep gesubstitueerde dibenz (b.f.)(1.4) oxazepinen. |
| GB1192812A (en) * | 1966-05-20 | 1970-05-20 | American Cyanamid Co | 2-Chloro-11-(1-Piperazinyl)Dibenz[b,f]-[1,4]Oxazepine, Non-Toxic Acid Addition Salts thereof, and Therapeutic Compositions containing said Oxazepine or Salts |
| US3597429A (en) * | 1968-02-15 | 1971-08-03 | Miles Lab | Derivatives of tetrazolyl alkanoic acids |
| GB1265866A (enExample) * | 1968-08-23 | 1972-03-08 | ||
| US3884922A (en) * | 1969-07-31 | 1975-05-20 | Yoshitomi Pharmaceutical | 11-(4-Pyridylalkyl-piperazino)-dibenzothiazepines |
| US4049809A (en) * | 1976-11-24 | 1977-09-20 | American Cyanamid Company | Solution of a oxazepine for oral or parenteral administration |
| GB1587128A (en) * | 1977-04-07 | 1981-04-01 | Hexachimie | Benzothiazepine derivatives |
| US5059600A (en) * | 1989-03-31 | 1991-10-22 | Yale University | Treating habit disorders |
| US5223497A (en) * | 1989-03-31 | 1993-06-29 | Yale University | Treating habit disorders |
| US5114942A (en) * | 1989-03-31 | 1992-05-19 | Yale University | Treating habit disorders |
| EP1047425A4 (en) * | 1997-12-17 | 2009-04-22 | Merck & Co Inc | INTEGRIN RECEPTOR ANTAGONISTS |
| US6890919B2 (en) * | 2001-06-26 | 2005-05-10 | Shitij Kapur | Atypical antipsychotic agents having low affinity for the D2 receptor |
| US7388954B2 (en) * | 2002-06-24 | 2008-06-17 | Freescale Semiconductor, Inc. | Method and apparatus for tone indication |
| WO2004056182A1 (en) * | 2002-12-20 | 2004-07-08 | Basf Aktiengesellschaft | Pesticidal dibenzo(hetero)azepine derivatives |
| WO2004064753A2 (en) * | 2003-01-23 | 2004-08-05 | Acadia Pharmaceuticals Inc | Use of n-desmethylclozapine to treat human neuropsychiatric disease |
| US20050250767A1 (en) * | 2003-01-23 | 2005-11-10 | Weiner David M | Use of N-desmethylclozapine to treat human neuropsychiatric disease |
| ES2286679T3 (es) | 2003-08-20 | 2007-12-01 | Eli Lilly And Company | Compuestos, procedimientos y formulaciones para la liberacion oral de un compuesto de peptido de tipo glucagon (glp)-1 o un peptido agonist a del receptor de melanocortina 4 (mc4). |
| EP1658273B1 (en) | 2003-08-20 | 2007-01-03 | Eli Lilly And Company | Compounds, methods and formulations for the oral delivery of a glucagon like peptide (glp)-1 compound or an melanocortin 4 receptor (mc4) agonist peptide |
| BRPI0417749A (pt) * | 2003-12-22 | 2007-04-10 | Acadia Pharm Inc | composto, método de sintese de composto, bibliotecas combinatórias, composições farmacêuticas e métodos de tratamento de disfunções neuropsiquiátricas |
| BRPI0509524A (pt) * | 2004-04-01 | 2007-09-18 | Acadia Pharm Inc | formas cristalinas de n-desmetilclozapina |
| WO2007053618A1 (en) * | 2005-10-31 | 2007-05-10 | Acadia Pharmaceuticals Inc. | Prodrugs of muscarinic agonists and methods of treatment of neuropsychiatric disorders |
| CA2728675A1 (en) | 2008-06-20 | 2009-12-23 | Astrazeneca Ab | Dibenzothiazepine derivatives and use thereof |
-
1965
- 1965-12-13 US US513553A patent/US3412193A/en not_active Expired - Lifetime
-
1966
- 1966-12-06 GB GB54597/66A patent/GB1129393A/en not_active Expired
- 1966-12-12 BE BE691049D patent/BE691049A/xx unknown
- 1966-12-12 FR FR87038A patent/FR1504326A/fr not_active Expired
- 1966-12-12 DE DE1620057A patent/DE1620057C3/de not_active Expired
- 1966-12-13 NL NL6617500A patent/NL6617500A/xx unknown
- 1966-12-13 CH CH1779166A patent/CH476001A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL6617500A (enExample) | 1967-06-14 |
| DE1620057A1 (de) | 1970-03-19 |
| DE1620057B2 (de) | 1977-10-06 |
| BE691049A (enExample) | 1967-05-16 |
| US3412193A (en) | 1968-11-19 |
| GB1129393A (en) | 1968-10-02 |
| FR1504326A (fr) | 1967-12-01 |
| CH476001A (de) | 1969-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee |